Synthesis 2021; 53(05): 943-953
DOI: 10.1055/s-0040-1705985
paper

Regioselective Functionalization of N-Fused Heteroaromatics via FeCl3-Catalyzed Nucleophilic Addition to Activated N-Heterocycles

Sung June Kim
,
Sunhee Lee
,
Ikyon Kim
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support.


Abstract

Broadening of nitrogen-fused heteroaromatic chemical space such as indolizine and pyrrolo[1,2-a]pyrazine was achieved via FeCl­3-catalyzed nucleophilic addition of these N-fused aromatic compounds to a wide range of azolinium systems generated in situ, leading to novel N-fused heteroaromatic scaffolds with dearomatized N-heterocyclic substituents regioselectively. Nucleophilic addition of indolizines and pyrrolo[1,2-a]pyrazines mainly occurred at the C1 position of the isoquinoliniums and at the C4 site of the quinoliniums.

Supporting Information



Publication History

Received: 06 October 2020

Accepted after revision: 26 October 2020

Publication Date:
08 December 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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